Green Synthesis and Study of Biological Activity of New Spiropyrrolooxindoles Using Ag@KF/Clinoptilolite Nanoparticles as Catalyst

Abstract

This study looked into the high yield production of new spiropyrrolooxindole derivatives. In order to create these new compounds, a multicomponent reaction involving isatin, malononitrile, alkyl 2,4-dioxo-4-(arylamino) butanoate derivatives, primary amines, and ethyl bromopyruvate was carried out in water at room temperature with catalytic amounts of Ag@KF/CP NPs acting as a high performance catalyst. The antioxidant property of new synthesized spiropyrrolooxindoles are owing to having NH group which was evaluated by two procedures. Also, the antimicrobial activity of new generated spiro isatins was evaluated by disk distribution process utilizing two kinds of Gram-negative bacteria and Gram-positive bacteria; proving bacterial growth was stopped by using of these compounds. Also, the catalytic activity of the green synthesized Ag@KF/CP NPs was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized NCs have very high and effective catalytic activity for organic pollutants within few seconds. Applied to the preparation of spiropyrrolooxindole derivatives, this method has short reaction times, high product yields, and the ability to separate catalyst and product using simple procedures.

Highlights

• The spiropyrrolooxindoles can be found in many molecules of biological or pharmaceutical interest.

• Multicomponent reactions (MCRs) are a more interesting type of reaction due to mixing three or more reactants in one-pot and generating one product and economically useful and environmentally secure than to multi-step methods.

• Carrying out synthesis of organic compounds in water media is very interesting because of water is cheap solvent, more available with high amounts.

Keywords:

• Ag@KF/CP
• biological activity
• spiropyrrolooxindoles
• multicomponent reaction
• primary amines
• alkyl 2,4-dioxo-4-(arylamino) butanoate
• malononitrile
• organic pollutants

Acknowledgement

We gratefully acknowledge Islamic Azad University, Iran because of spiritual support.